Richard Branson made headlines in 2010 when he boasted that Virgin Hotels, his new boutique hospitality brand, would shake up the industry. The first property was projected to open within 18 months, with up to two dozen more operating within seven years.

Reality, so far, hasn’t lived up to those lofty expectations. Nearly four years after Mr. Branson’s boast, Virgin Hotels still hasn’t opened a single property, and has had to deal with the departure of two top executives.

The brand’s maiden hotel is due to open in Chicago in the fall—a year behind schedule—and has been marred by cost overruns.